A Domino Palladium-Catalyzed C–C and C–O Bonds Formation via Dual O–H Bond Activation: Synthesis of 6,6-Dialkyl-6H-benzo[c]chromenes
- 11 January 2012
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (2), 628-631
- https://doi.org/10.1021/ol2032625
Abstract
An efficient Pd-catalyzed domino reaction of α,α-dialkyl-(2-bromoaryl)methanols to 6,6-dialkyl-6H-benzo[c]chromenes is presented. Their formation can be explained via a five membered Pd(II)-cycle that efficiently involves a domino homocoupling with the second molecule, β-carbon cleavage, and finally intramolecular Buchwald–Hartwig cyclization. This domino process effectively involves breaking of five σ-bonds (2C–Br, 2O–H, and a C–C) and formation of two new σ-bonds (C–C and C–O). This mechanistic pathway is unprecedented and further illustrates the power of transition metal catalysis.Keywords
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